Title: Middletown, NY Cottage Rentals from $197 | Expedia.com [Middletown Travel Guide](https://expedia.com/Middletown.dx8864)[Hotels in Middletown](https://expedia.com/Middletown-Hotels.d8864.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.com/Middletown-Vacation-Rentals.d8864.Travel-Guide-VacationRentals)[Flights to Middletown](https://expedia.com/Cheap-Flights-To-Middletown.d8864.Travel-Guide-Flights)[Things to do in Middletown](https://expedia.com/Things-To-Do-In-Middletown.d8864.Travel-Guide-Activities)[Car Rentals in Middletown](https://expedia.com/Car-Rentals-In-Middletown.d8864.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.com/Middletown.d8864.Destination-Travel-Guides) ![Route 17 in ny is a great road to view the fall foliage](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Vincent Ramundo ![](https://images.trvl-media.com/place/8005/8b2c54c4-af30-4521-9b56-3bdf0a8d1a15.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=8864&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middletown cottages ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w919h683x47y0-1b7c08f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w906h683x59y0-c6be118f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-6b740411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/100000000/99270000/99261600/99261544/w506h683x259y0-81ebd497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hello Small Stone [](https://www.expedia.com/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information) Middletown 9.6/10 Exceptional (5 reviews) "The house was great. It was nice to sit and relax by the small pond in the back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John H. $384 nightly $434 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Middletown-Hotels-Hello-Small-Stone.h99261544.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/dabdeda4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/cd189b6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/4fbee988.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83440000/83439100/83439008/7cf93160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) Kerhonkson 9.4/10 Exceptional (12 reviews) "Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick S. $195 nightly $197 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Kerhonkson-Hotels-Dream-Cottage-In-The-Gunks.h83439008.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/dd263f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/54004000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/3008d822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/79000000/78140000/78138100/78138015/eb48d384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Farm Cottage Escape, 10 Min from LEGOLAND [](https://www.expedia.com/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) Goshen 9.8/10 Exceptional (13 reviews) "Beautiful location. We really enjoyed seeing the deer in the field every morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron M. $281 nightly $293 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Goshen-Hotels-Relaxing-Farm-Cottage-Escape.h78138015.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/1e61a43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/68236176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/e668d22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82540000/82537300/82537288/5178d297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around [](https://www.expedia.com/Sparrow-Bush-Hotels-Serene-Lakeside-Oasis-Fast-WiFi-15-Hrs-From-NYC.h82537288.Hotel-Information) Sparrow Bush 9.4/10 Exceptional (11 reviews) "A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas G. $260 nightly $294 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Sparrow-Bush-Hotels-Serene-Lakeside-Oasis-Fast-WiFi-15-Hrs-From-NYC.h82537288.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/3a9ea66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/dfec5e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/5ed95c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34350000/34345200/34345199/e56d490f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands [](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) Fort Montgomery 9.8/10 Exceptional (131 reviews) "Amazing place Thanks for the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julien C. $269 nightly $304 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Fort-Montgomery-Hotels-Serene-Mountain-Top-Views-Overlooking-Hudson-River-And-Surrounding-Highlands.h34345199.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3379h2254x65y113-3bf6be6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w3378h2246x65y117-b9d7217d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/70357fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777320/w2352h3136x64y187-6f5dc167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike [](https://www.expedia.com/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) Vernon Township 8.8/10 Excellent (3 reviews) "House was beautiful! Airy, cool and bedrooms were comfortable! Such a cute cottage and outdoor fire pit was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cherlyn I. $423 nightly $478 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Vernon-Hotels-Luxe-10-Guest-Cottage-SkiGolfFire-PitLakesHike.h108777320.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20®ionId=8864&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VACATION_HOME) Villas [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=VILLA) Condos [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APARTMENT) Chalets [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=CHALET) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Middletown%2C+New+York%2C+United+States+of+America®ionId=8864&latLong=41.445927%2C-74.422935&adults=2&startDate=2026-05-06&d1=2026-05-06&endDate=2026-05-09&d2=2026-05-09&lodging=APART_HOTEL) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Cottages.d8864-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Cottages.d8864-aaCottages.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/77a42b8a_y.jpg) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen 10/10 Excellent "Clean room" [](https://expedia.com/Middletown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Middletown.h4098.Hotel-Information) ![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d_y.jpg) ### The Kartrite Resort & Indoor Waterpark 10/10 Excellent "Great stay" [](https://expedia.com/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Hampton Inn Harriman Woodbury](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9_y.jpg) ### Hampton Inn Harriman Woodbury 10/10 Excellent "Room was clean- " [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![The Thayer Hotel at West Point](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f_y.jpg) ### The Thayer Hotel at West Point 10/10 Excellent "Everything about the Thayer is amazing. From the food to the people to the room to the views. Love love love!!" [](https://expedia.com/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Sleep Inn & Suites Monroe - Woodbury](https://images.trvl-media.com/lodging/21000000/20600000/20597600/20597588/0db56af9_y.jpg) ### Sleep Inn & Suites Monroe - Woodbury 10/10 Excellent "Great value " [](https://expedia.com/Newburgh-Hotels-Sleep-Inn-Suites-Monroe-Woodbury.h20597588.Hotel-Information) ![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49_y.jpg) ### Resorts World Catskills Casino 10/10 Excellent "Staff was great " [](https://expedia.com/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Hampton Inn by Hilton Middletown](https://images.trvl-media.com/lodging/1000000/290000/282000/281932/8c9a3fbd_y.jpg) ### Hampton Inn by Hilton Middletown 10/10 Excellent "Staff was friendly and efficient. Bed comfy, super quiet & safe. I stayed only to sleep for a few hours during a snowstorm to be close to the hospital down the road so I didn’t have to drive far in the snow. It was expensive but worth the safe commute to work. Their parking lot was plowed and accessible. " [](https://expedia.com/Newburgh-Hotels-Hampton-Inn-By-Hilton-Middletown.h281932.Hotel-Information) ![Overlook Lodge at Bear Mountain](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6_y.jpg) ### Overlook Lodge at Bear Mountain 10/10 Excellent "yup" [](https://expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Tru by Hilton Middletown](https://images.trvl-media.com/lodging/37000000/36250000/36247800/36247736/935c6486_y.jpg) ### Tru by Hilton Middletown 10/10 Excellent "Yes I enjoyed my stay" [](https://expedia.com/Newburgh-Hotels-Tru-By-Hilton-Middletown.h36247736.Hotel-Information) ## Find out more about Middletown ## Middletown Cottages information | Number of reviews | 156 | | ----------------- | ------------ | | Accommodation | 134 Cottages | | Lowest Price | $197 | | Highest Price | $478 | ## Frequently asked questions ### Why book your cottage in Middletown with Expedia? ### How can I find cheap cottages in Middletown? ### What is there to do in Middletown near my cottage? ## Explore a world of travel with Expedia - 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